Aluminium lithium hydride → 3-(5-Fluoro-2-methoxyphenyl)-3-methylbutan-1-ol

HRID 400628Notes

Reaction equation

HRID 400628 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[O:8][C:9](=O)[CH2:10][C:11]([C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[O:21][CH3:22])([CH3:13])[CH3:12]>C1COCC1.C(OCC)C>[F:20][C:18]1[CH:17]=[CH:16][C:15]([O:21][CH3:22])=[C:14]([C:11]([CH3:12])([CH3:13])[CH2:10][CH2:9][OH:8])[CH:19]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57809938Methyl 3-methyl-3-(2-methoxy-5-fluorophenyl)butanoate

Product 1

HCID 578097383-(5-Fluoro-2-methoxyphenyl)-3-methylbutan-1-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (1.64 g) in 100 mL of THF stirred under argon was added dropwise over 30 minutes a solution of the above 3-(5-fluoro-2-methoxyphenyl)-3-methylbutyric acid methyl ester in 10 mL of THF (vigorous reaction). The mixture was stirred at room temperature overnight. The reaction was diluted with 200 mL of diethyl ether and quenched by the addition of 3 mL of water (added cautiously) and 3 mL of acetic acid. The mixture was filtered through diatomaceous earth and washed through with diethyl ether. Evaporation of the solvent gave 10.8 g of 3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-ol, which was used without additional purification.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customquenched by the addition of 3 mL of water (
  3. additionadded cautiously) and 3 mL of acetic acid
  4. filtrationThe mixture was filtered through diatomaceous earth
  5. washwashed through with diethyl ether
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f68f8ed635524fa0ad827e9d633783b5
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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